Headless Horseman Hussle 2026 — Sleepy Hollow, IL

Date
September 20, 2026
Location
Sleepy Hollow, IL
Venue
898 Glen Oak Dr
Start Time
9:00 AM
Entry Fee
$30.00
Events
Headless Horseman Hussle 5k
Includes
T-Shirt
Register NowRegistration Open

The Headless Horseman Hustle takes place at 898 Glen Oak Dr in Sleepy Hollow, Illinois on September 20, 2026. This running event features a 5K distance and starts at 9:00 AM. The entry fee is $30.00. Whether you're training through the fall season or looking for a local race to test your fitness, this 5K offers a straightforward option for runners in the area. Plan your travel accordingly if you're coming from out of town, and arrive early to handle registration before the 9:00 AM start.

From the Race Organizer
Join us for the Headless Horseman Hussle 5K, a fun and energizing community race through the beautiful Village of Sleepy Hollow, Illinois! Whether you're a seasoned runner, a casual jogger, or just want to enjoy a morning walk with friends and family, this event is for everyone. This race is proudly hosted as a fundraiser for the Sleepy Hollow Elementary PTC, with all proceeds going directly towards supporting students, teachers, and school programs in our community. The course will take participants through scenic neighborhood streets making it a perfect event to enjoy the outdoors while giving back. Bring your friends, family, and school spirit as we run, walk, and cheer together for a great cause. Race highlights: 5k run/walk open to all ages and abilities Optional 1k walk for younger participates Community-focused and family-friendly event Proceeds benefit the PTC and local school programs A great way to support education while staying active Come out, get moving, and help make a difference for our students!

Hotels Near This Race

Find accommodation close to the start line in Sleepy Hollow, IL. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.

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Headless Horseman Hussle 2026 — Sleepy Hollow, IL

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Race Travel Insurance

Don't forget travel insurance for September 20.

You've trained for months and booked a trip to Sleepy Hollow, IL. A pre-race injury, a delayed flight, or a family emergency can derail the whole thing. Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it, and may cover medical costs if something goes wrong on the course. Plans typically only run 5-7% of your total trip cost — and running events are covered under standard plans with no additional coverage needed.

  • Trip cancellation up to 100% of prepaid costs
  • Running events covered under standard plans — no add-ons needed
  • Trip interruption up to 150% of non-refundable costs
  • Emergency medical up to $250,000
  • Cancel For Any Reason add-on available
  • 24/7 real-time support
Get a Quote — Faye Travel Insurance

Affiliate links — we may earn a commission at no cost to you. Coverage terms vary by state and plan. Review policy details before purchase.

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Frequently Asked Questions

When is Headless Horseman Hussle 2026 — Sleepy Hollow, IL?

Headless Horseman Hussle 2026 — Sleepy Hollow, IL takes place on September 20, 2026. The race is held in Sleepy Hollow, Illinois.

Where is Headless Horseman Hussle 2026 — Sleepy Hollow, IL held?

Headless Horseman Hussle 2026 — Sleepy Hollow, IL is held at 898 Glen Oak Dr in Sleepy Hollow, Illinois.

Where can I find hotels near Headless Horseman Hussle 2026 — Sleepy Hollow, IL?

RaceHotelFinder shows hotels sorted by distance from the race venue in Sleepy Hollow. Use the map or list view on this page to compare options and book race weekend accommodation.